Trimethyl borate → [4-(Difluoromethyl)phenyl]boronic acid

HRID 19831Notes

Reaction equation

[F:1][CH:2]([F:10])[C:3]1[CH:8]=[CH:7][C:6](I)=[CH:5][CH:4]=1.C([Mg]Cl)(C)C.[B:16](OC)([O:19]C)[O:17]C>>[F:1][CH:2]([F:10])[C:3]1[CH:8]=[CH:7][C:6]([B:16]([OH:19])[OH:17])=[CH:5][CH:4]=1

Participants

Reactant 3

HCID 8470Trimethyl borate

HCID 463117371-(Difluoromethyl)-4-iodobenzene

HCID 178418918HCID 178418918, compound

Product 1

HCID 20777176[4-(Difluoromethyl)phenyl]boronic acid

Procedure

In a departure from the procedure described above the compound is prepared from 4-difluoromethyl-1-iodo-benzene (prepared from 4-iodobenzaldehyde using diethylaminosulfurtrifluoride (DAST) in dichloromethane) using iPrMgCl to generate the arylmetal compound and trapping this intermediate with trimethyl borate.

Sources & evidence

ORD record: ord-087999f7e0d549caa6d74fe79b97b3d8
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07745414B2

Reaction notes

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